Undergraduate → Organic chemistry ↓
Functional Group
Introduction to functional groups
In organic chemistry, functional groups are specific groups of atoms within molecules that have characteristic properties and chemical reactivity. They are major determinants of the properties of organic compounds. When we understand functional groups, we can predict what types of chemical reactions an organic compound can undergo. The simplest organic molecules are hydrocarbons, which contain only carbon and hydrogen. By replacing one or more hydrogen atoms with functional groups, we can obtain a huge variety of organic compounds.
Understanding functional groups
The functional group can be thought of as an atom or group of atoms that replaces hydrogen in a hydrocarbon. Often, the functional group is responsible for the chemical reactions of the molecule. For example, alcohols contain the functional group -OH (hydroxyl group), and this group is responsible for the characteristic reactions of alcohols.
Common functional groups
1. Hydroxyl group (-OH)
The hydroxyl group is characterized by an oxygen atom bonded to a hydrogen atom:
-OH
This is the defining characteristic of alcohol. Ethanol, a common alcohol, has the formula C2H5OH:
CH3CH2OH
2. Carbonyl group (C=O)
The carbonyl group contains a double bond between a carbon atom and an oxygen atom:
C=O
The carbonyl group is a defining feature of several functional classes, such as ketones and aldehydes.
In ketones the carbonyl group is bonded to two carbon atoms:
RC(=O)-R'
In aldehydes, at least one of the groups attached to the carbonyl carbon is a hydrogen atom:
RC(=O)H
3. Carboxyl group (-COOH)
The carboxyl group is a characteristic functional group of carboxylic acids and consists of a carbonyl group linked to a hydroxyl group:
-COOH
For example, the structural formula of acetic acid is:
CH3COOH
4. Amino group (-NH2)
The amino group consists of a nitrogen atom bonded to two hydrogen atoms and this is a characteristic of amines:
-NH2
For example, in methylamine:
CH3NH2
5. Sulfhydryl group (-SH)
The sulfhydryl group is a functional group equivalent to the hydroxyl group, containing a sulfur atom in place of an oxygen atom:
-SH
This group is characteristic of thiols, as in ethanethiol:
CH3CH2SH
6. Phosphate group (-PO4)
A phosphate group is a phosphorus atom bonded to four oxygen atoms and is seen in biomolecules such as ATP:
-PO4
It plays an important role in molecular biology, as the energy currency of cells involves phosphate transfer.
Importance of functional groups
Functional groups are important for classifying organic compounds and predicting chemical reactions. By identifying the functional group, chemists can infer a lot about the molecule's properties and potential reactivity. They also provide a systematic way to name organic compounds.
For example, alcohols react differently from alkenes, even though both are made from similar hydrocarbon structures. Alcohols undergo reactions typical of the hydroxyl group, which involves oxygen and hydrogen atoms.
Naming organic compounds using functional groups
The naming of organic compounds follows a systematic naming method developed by the International Union of Pure and Applied Chemistry (IUPAC). Here, functional groups are an integral part of the naming process. The presence of a functional group is often followed by a suffix or prefix in the name of the compound:
- Alcohol: The suffix
-ol
is added, e.g., ethanol. - Aldehyde: The suffix
-al
is added, for example, formaldehyde. - Carboxylic acids: The suffix
-oic acid
is added, for example, acetic acid.
Functional groups in chemical reactions
Functional groups predict how molecules react chemically. Knowing the functional group helps chemists predict what specific reactions a molecule might undergo. For example, knowing that a compound is an alcohol suggests that it might undergo oxidation reactions to form an aldehyde or ketone.
Some of the reactions involving functional groups are as follows:
- Hydration of alkenes: Alkene
C=C
groups react with water in the presence of acids to form alcohols. - Esterification: Carboxylic acids react with alcohols to form esters and water.
- Reduction of carbonyl: Carbonyl compounds like aldehydes and ketones can be reduced to alcohols using reducing agents like NaBH4.
Summary
Functional groups are fundamental to organic chemistry, determining the physical and chemical properties of molecules. They allow chemists to classify carbon compounds and predict how they might react in various chemical processes. Understanding functional groups is a step toward mastering organic chemistry and is important for fields as diverse as pharmaceuticals, materials science, and biochemistry.